Notorious B.I.G. began rapping when he was a teenager. He entertained people on the streets and performed with local groups the Old Gold Brothers and the Techniques. After being released from jail, Wallace made a demo tape under the name Biggie Smalls, a reference to a character in the 1975 film Let’s Do It Again as well as his stature; he stood at 6 feet 3 inches (1.91 m) and weighed as much as 300 to 380 pounds (140–170 kg) according to differing accounts. The tape was reportedly made with no serious intent of getting a recording deal, but was promoted by New York-based DJ Mister Cee, who had previously worked with Big Daddy Kane, and was heard by the editor of The Source.
In March 1992, Wallace was featured in The Source’s Unsigned Hype column, dedicated to aspiring rappers, and was invited to produce a recording with other unsigned artists in a move that was reportedly uncommon at the time. The demo tape was heard by Uptown Records A&R and record producer Sean Combs, who arranged for a meeting with Wallace. He was signed to Uptown immediately and made an appearance on label mates, Heavy D & the Boyz’ “A Buncha Niggas” (from the album Blue Funk). Soon after signing his recording contract, Combs was fired from Uptown and started a new label. Wallace followed and in mid-1992, signed to Combs’ new imprint label, Bad Boy Records. On August 8, 1993, Wallace’s longtime girlfriend gave birth to his first child, T’yanna. He continued selling drugs after the birth to support his daughter financially. Once Combs discovered this, he forced Wallace to quit.
Later in the year, Wallace gained exposure on a remix to Mary J. Blige’s single “Real Love”, under the pseudonym The Notorious B.I.G. He recorded under this name for the remainder of his career, after finding the original moniker “Biggie Smalls” was already in use. “Real Love” peaked at No. 7 on the Billboard Hot 100 chart and was followed by a remix of Blige’s “What’s the 411?”. He continued this success, to a lesser extent, on remixes with Neneh Cherry (“Buddy X”) and reggae artist Super Cat (“Dolly My Baby”, also featuring Combs) in 1993. In April 1993, his solo track, “Party and Bullshit”, appeared on the Who’s the Man? soundtrack. In July 1994, he appeared alongside LL Cool J and Busta Rhymes on a remix to label mate Craig Mack’s “Flava in Ya Ear”, reaching No. 9 on the Hot 100.